CA2822694C - Isomere de cardiogenine purifie et procedes apparentes - Google Patents

Isomere de cardiogenine purifie et procedes apparentes Download PDF

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Publication number
CA2822694C
CA2822694C CA2822694A CA2822694A CA2822694C CA 2822694 C CA2822694 C CA 2822694C CA 2822694 A CA2822694 A CA 2822694A CA 2822694 A CA2822694 A CA 2822694A CA 2822694 C CA2822694 C CA 2822694C
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Canada
Prior art keywords
cardiogenin
methanol
compound
column
huya
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Application number
CA2822694A
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English (en)
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CA2822694A1 (fr
Inventor
Andreas KYAS
Ernst Freund
Oliver Schlorke
James R. Paterniti
Gary Elliott
Jorg LILL
Lars ROGALL
Dario MENIA
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Huya Bioscience International LLC
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Huya Bioscience International LLC
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Publication of CA2822694A1 publication Critical patent/CA2822694A1/fr
Application granted granted Critical
Publication of CA2822694C publication Critical patent/CA2822694C/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/32—Unsaturated compounds containing hydroxy or O-metal groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7024—Esters of saccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C07H1/08—Separation; Purification from natural products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
    • A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Mycology (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Botany (AREA)
  • Medical Informatics (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Steroid Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)

Abstract

L'invention concerne un isomère majeur de cardiogénine qui est obtenu à partir d'un extrait de méthanol de Geum japonicum et séparé de son isomère mineur. La séparation des deux isomères peut être obtenue par une chromatographie en phase chirale, par exemple, à l'aide d'une colonne Chiralpak® IC. La pureté de l'isomère majeur de cardiogénine isolé peut être encore augmentée par cristallisation, fournissant une isomère majeur de cardiogénine isolé ayant une pureté HPLC aussi élevée que 98,97 % (a/a) à 210 nm et une puissance de 95,50 % (p/p).
CA2822694A 2010-12-23 2011-12-21 Isomere de cardiogenine purifie et procedes apparentes Active CA2822694C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201061426929P 2010-12-23 2010-12-23
US61/426,929 2010-12-23
PCT/US2011/066469 WO2012088264A2 (fr) 2010-12-23 2011-12-21 Isomère de cardiogénine purifié et procédés apparentés

Publications (2)

Publication Number Publication Date
CA2822694A1 CA2822694A1 (fr) 2012-06-28
CA2822694C true CA2822694C (fr) 2020-08-04

Family

ID=46314885

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2822694A Active CA2822694C (fr) 2010-12-23 2011-12-21 Isomere de cardiogenine purifie et procedes apparentes

Country Status (8)

Country Link
US (2) US20130345159A1 (fr)
EP (1) EP2655390B1 (fr)
JP (3) JP2014500328A (fr)
KR (1) KR20140010936A (fr)
CN (2) CN106565814A (fr)
AU (2) AU2011349207A1 (fr)
CA (1) CA2822694C (fr)
WO (1) WO2012088264A2 (fr)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2209222A1 (fr) * 1997-06-27 1998-12-27 Keng-Yeow Sim Inhibiteurs de la protease retrovirale
US5916919A (en) * 1997-06-27 1999-06-29 Dalhousie University Retrovirus protease inhibitors
US7713942B2 (en) * 2001-04-04 2010-05-11 Nordic Vaccine Technology A/S Cage-like microparticle complexes comprising sterols and saponins for delivery of polynucleotides
WO2007049089A1 (fr) * 2005-10-27 2007-05-03 Lead Billion Limited Utilisation de ga et de nif pour traiter des tissus ischemiques ou endommages
JP4950996B2 (ja) * 2005-10-27 2012-06-13 リード ビリオン リミテッド 虚血性心疾患の治療に有用な、血管新生／血行再建のための医薬組成物及び方法
CN101502542B (zh) * 2009-03-17 2011-01-05 江南大学 一种猕猴桃根提取物的提取方法及其抗肝损伤的应用
WO2010143059A1 (fr) * 2009-06-12 2010-12-16 Generex Pharmaceuticals, Inc. Compositions et procédé de préparation de compositions pour prévenir et traiter l'hypertension

Also Published As

Publication number Publication date
WO2012088264A2 (fr) 2012-06-28
JP2019048867A (ja) 2019-03-28
AU2017200924A1 (en) 2017-03-02
EP2655390B1 (fr) 2019-03-27
EP2655390A4 (fr) 2014-05-28
US20130345159A1 (en) 2013-12-26
AU2011349207A1 (en) 2013-07-11
JP2017110012A (ja) 2017-06-22
CN106565814A (zh) 2017-04-19
KR20140010936A (ko) 2014-01-27
AU2017200924B2 (en) 2018-06-14
WO2012088264A3 (fr) 2013-01-17
CA2822694A1 (fr) 2012-06-28
EP2655390A2 (fr) 2013-10-30
CN103282371A (zh) 2013-09-04
US20160207869A1 (en) 2016-07-21
JP2014500328A (ja) 2014-01-09

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